91Ó°ÊÓ

Question: Draw a stepwise, detailed mechanism for the following reaction.

Question: Friedel-Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl₃ affords sec-butylbenzene.

1. How many stereogenic centers are present in the product?
2. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.

Question: Although two products (A and B) are possible when naphthalene undergoes electrophilic aromatic substitution, only A is formed. Draw resonance structures for the intermediate carbocation to explain why this is observed.

Question: Synthesize each compound from toluene and any other organic or inorganic reagents.